Synthesis of Chiral Lactones and Triols from a-Acetyl-g-butyrolactones by Use of Bakes's YEast

Heterocycles ◽  
1992 ◽  
Vol 33 (2) ◽  
pp. 489 ◽  
Author(s):  
Mitsuhiro Takeshita ◽  
Hiroko Yanagihara ◽  
Sachiko Yoshida
Keyword(s):  
Chiral Lactones

Stereochemistry of terpene derivatives. Part 5: Synthesis of chiral lactones fused to a carane system—insect feeding deterrents

2006 ◽  
Vol 17 (1) ◽  
pp. 124-129 ◽  
Author(s):  
Bożena Frąckowiak ◽  
Katarzyna Ochalik ◽  
Agata Białońska ◽  
Zbigniew Ciunik ◽  
Czesław Wawrzeńczyk ◽  
...  
Keyword(s):  
Feeding Deterrents ◽  
Insect Feeding ◽  
Chiral Lactones ◽  
Insect Feeding Deterrents ◽  
Terpene Derivatives

ChemInform Abstract: Useful Chiral Lactones Derived from cis-Bicyclo(3.3.0)octan-3,7-dione via Asymmetric Deprotonation.

ChemInform ◽  
2010 ◽  
Vol 22 (8) ◽  
pp. no-no
Author(s):  
J. LEONARD ◽  
J. D. HEWITT ◽  
D. OUALI ◽  
S. K. RAHMAN ◽  
S. J. SIMPSON ◽  
...  
Keyword(s):  
Chiral Lactones

ChemInform Abstract: Chiral Lactones by Asymmetric Hydrogenation - A Step Forward in (+)-Biotin Production

ChemInform ◽  
2011 ◽  
Vol 42 (23) ◽  
pp. no-no
Author(s):  
Werner Bonrath ◽  
Reinhard Karge ◽  
Thomas Netscher ◽  
Felix Roessler ◽  
Felix Spindler
Keyword(s):  
Asymmetric Hydrogenation ◽  
Chiral Lactones

Fusion proteins of an enoate reductase and a Baeyer-Villiger monooxygenase facilitate the synthesis of chiral lactones

2017 ◽  
Vol 398 (1) ◽  
pp. 31-37 ◽  
Author(s):  
Christin Peters ◽  
Florian Rudroff ◽  
Marko D. Mihovilovic ◽  
Uwe T. Bornscheuer
Keyword(s):  
Fusion Protein ◽  
Fusion Proteins ◽  
Reaction Rates ◽  
Cascade Reactions ◽  
Product Formation ◽  
Similar Reaction ◽  
Enzyme Cascade ◽  
Enoate Reductase ◽  
Chiral Lactones

Abstract Nature uses the advantages of fusion proteins for multi-step reactions to facilitate the metabolism in cells as the conversion of substrates through intermediates to the final product can take place more rapidly and with less side-product formation. In a similar fashion, also for enzyme cascade reactions, the fusion of biocatalysts involved can be advantageous. In the present study, we investigated fusion of an alcohol dehydrogenase (ADH), an enoate reductase (ERED) and a Baeyer-Villiger monooxygenase (BVMO) to enable the synthesis of (chiral) lactones starting from unsaturated alcohols as substrates. The domain order and various linkers were studied to find optimal conditions with respect to expression levels and enzymatic activities. Best results were achieved for the ERED xenobiotic reductase B (XenB) from Pseudomonas putida and the cyclohexanone monooxygenase (CHMO) from Acinetobacter sp., whereas none of the ADHs studied could be fused successfully. This fusion protein together with separately supplied ADH resulted in similar reaction rates in in vivo biocatalysis reactions. After 1.5 h we could detect 40% more dihydrocarvone lactone in in vivo reactions with the fusion protein and ADH then with the single enzymes.

ChemInform Abstract: Preparation of Chiral Lactones from L-Lactic Acid via (S)-γ-Methyltetronic Acid (I).

ChemInform ◽  
1988 ◽  
Vol 19 (16) ◽  
Author(s):  
S. BRANDAENGE ◽  
K. JANSBO ◽  
T. MINASSIE
Keyword(s):  
Lactic Acid ◽  
Chiral Lactones

scholarly journals Biosynthesis of Lactones From Diols Mediated by an Artificial Flavin

2021 ◽  
Author(s):  
Xiaowang Zhang ◽  
Zhuotao Tan ◽  
Chaojian Li ◽  
Siyu Qi ◽  
Mengjiao Xu ◽  
...  
Keyword(s):  
Product Yield ◽  
Product Inhibition ◽  
Phase System ◽  
Regeneration System ◽  
Two Phase ◽  
Promising Alternative ◽  
Liver Alcohol Dehydrogenase ◽  
Horse Liver ◽  
Valuable Compounds ◽  
Chiral Lactones

Abstract Background: Lactones are important compounds in the field of medicine, material and chemical industry. One of the promising accesses to these flexible scaffolds is NAD(P)+-dependent alcohol dehydrogenases-catalyzed oxidative lactonization of diols, which relies on the construction of an efficient NAD(P)+ regeneration system. Results: In this study, a novel system combining horse liver alcohol dehydrogenase (HLADH) with the synthetic bridged flavin cofactor was established for biosynthesis of lactones. The reaction conditions of this system were optimized and a variety of lactones including chiral lactones were efficiently obtained from various diols. Compared to the previously reported NAD(P)+-regeneration systems, this system showed better regeneration efficiency and product yield. A two-phase system was further applied to solve the problem of product inhibition, and 80% yield was obtained at the condition of 300 mM substrate.Conclusions: This study provides an efficient method to synthesis of lactones from diols under mild conditions. We believe this system will be a promising alternative to promote the synthesis of other valuable compounds.

scholarly journals Biosynthesis of lactones from diols mediated by an artificial flavin

2021 ◽  
Vol 8 (1) ◽  
Author(s):  
Xiaowang Zhang ◽  
Zhuotao Tan ◽  
Chaojian Li ◽  
Siyu Qi ◽  
Mengjiao Xu ◽  
...  
Keyword(s):  
Product Yield ◽  
Product Inhibition ◽  
Phase System ◽  
Regeneration System ◽  
Two Phase ◽  
Promising Alternative ◽  
Liver Alcohol Dehydrogenase ◽  
Horse Liver ◽  
Valuable Compounds ◽  
Chiral Lactones

Abstract Background Lactones are important compounds in the field of medicine, material and chemical industry. One of the promising accesses to these flexible scaffolds is NAD(P)+-dependent alcohol dehydrogenases-catalyzed oxidative lactonization of diols, which relies on the construction of an efficient NAD(P)+ regeneration system. Results In this study, a novel system combining horse liver alcohol dehydrogenase (HLADH) with the synthetic bridged flavin cofactor was established for biosynthesis of lactones. The reaction conditions of this system were optimized and a variety of lactones including chiral lactones were efficiently obtained from various diols. Compared to the previously reported NAD(P)+-regeneration systems, this system showed better regeneration efficiency and product yield. A two-phase system was further applied to solve the problem of product inhibition, and 80% yield was obtained at the condition of 300 mM substrate. Conclusions This study provides an efficient method to synthesis of lactones from diols under mild conditions. We believe this system will be a promising alternative to promote the synthesis of other valuable compounds. Graphic abstract

Bakers' Yeast Reduction of γ and δ Ketonitriles: Intermediates for the Synthesis of (S)-5-Hexanolide and Other Chiral Lactones

1991 ◽  
Vol 21 (12-13) ◽  
pp. 1321-1329 ◽  
Author(s):  
Aravamudan Gopalan ◽  
Richard Lucero ◽  
Hollie Jacobs ◽  
Kent Berryman
Keyword(s):  
Chiral Lactones
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